Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Pool Hot Tub

    $17,975 to $27,561/night

  2. ESTATE
    Mauna Kea Bluffs #5: La Ikena O Komohana*

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    Kamuela, HI

    Pool Hot Tub

    $10,240 to $12,620/night

  3. HOUSE
    Kalina at Hapuna Beach

    Kalina at Hapuna Beach

    Kamuela, HI

    Pool Hot Tub

    $4,194 to $7,190/night

  4. ESTATE
    Mauna Kea Resort Bluffs 22- The Beach House

    Mauna Kea Resort Bluffs 22- The Beach House

    Kamuela, HI

    Pool Hot Tub

    $3,695 to $6,075/night

  5. VILLA
    Wailea Inn Maui

    Wailea Inn Maui

    Kihei, HI

    $3,248 to $5,568/night

  6. APARTMENT
    Blue Lagoon*

    Blue Lagoon*

    Kamuela, HI

    $2,743 to $6,408/night

  7. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Pool Hot Tub

    $2,203 to $4,290/night

  8. HOUSE
    Hale Nui

    Hale Nui

    Kaanapali, HI

    Pool Hot Tub
    FREE CANCELLATION

    $2,000 to $4,750/night

  9. HOUSE
    Wilikoki House

    Wilikoki House

    Hanalei, HI

    FREE CANCELLATION

    $1,870 to $2,494/night

  10. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    Lahaina, HI

    Hot Tub
    FREE CANCELLATION

    $1,869 to $3,125/night

  11. VILLA
    Hale Waiulu

    Hale Waiulu

    Kailua Kona, HI

    Pool Hot Tub

    $1,791 to $5,992/night

  12. CONDOMINIUM
    WAILEA ELUA, #1305^

    WAILEA ELUA, #1305^

    Wailea, Maui, HI

    Pool Hot Tub

    $1,761 to $2,076/night

  13. VILLA
    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps To Beach

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    Kihei, HI

    $1,734 to $3,392/night

  14. VILLA
    Makena Aloha Estate

    Makena Aloha Estate

    Lahaina, HI

    Pool Hot Tub

    $1,722 to $3,075/night

  15. HOUSE
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    $1,661 to $2,429/night

  16. HOUSE
    Hale Pua

    Hale Pua

    Kailua Kona, HI

    Pool Hot Tub

    $1,635 to $2,364/night

  17. HOUSE
    Laulea Kailani Villa (KAUAI)

    Laulea Kailani Villa (KAUAI)

    Princeville, HI

    Pool

    $1,553 to $3,338/night

  18. HOUSE
    INDO LOTUS BEACH HOUSE

    INDO LOTUS BEACH HOUSE

    Kihei, Maui, HI

    Hot Tub

    $1,458 to $2,694/night

  19. APARTMENT
    Blue Oasis*

    Blue Oasis*

    Kamuela, HI

    $1,434 to $3,267/night

  20. HOUSE
    Moloa'a Bay Villa and Cottage

    Moloa'a Bay Villa and Cottage

    Anahola, HI

    $1,413 to $1,906/night

  21. HOUSE
    House of the Turtle at Champion Ridge, Mauna Lani (CR 18)

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18...

    Kamuela, HI

    Pool Hot Tub

    $1,373 to $4,069/night

  22. HOUSE
    Kona Bay Bliss

    Kona Bay Bliss

    Kailua Kona, HI

    Pool Hot Tub

    $1,372 to $2,014/night

  23. HOUSE
    Makalae

    Makalae

    Koloa, HI

    $1,303 to $1,404/night

  24. HOUSE
    Kona Bubbles

    Kona Bubbles

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,253 to $1,395/night

  25. HOUSE
    Moloa'a Bay Villa

    Moloa'a Bay Villa

    Anahola, HI

    $1,208 to $1,413/night

  26. HOUSE
    Lau'lea at the Mauna Lani*

    Lau'lea at the Mauna Lani*

    Kamuela, HI

    Pool Hot Tub

    $1,195 to $4,289/night

  27. ESTATE
    Diamond Head Tiki Estate

    Diamond Head Tiki Estate

    Honolulu, HI

    Pool
    FREE CANCELLATION

    $1,188 to $3,063/night

  28. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, HI

    Pool Hot Tub

    $1,168 to $2,876/night

  29. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    $1,160 to $3,420/night

  30. HOUSE
    Hale Lani

    Hale Lani

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $1,155 to $1,533/night

  31. HOUSE
    Pu'uwai Hale

    Pu'uwai Hale

    Princeville, HI

    $1,152 to $1,645/night

  32. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Pool Hot Tub

    $1,150 to $1,605/night

  33. HOUSE
    Ke Kailani Hale A2

    Ke Kailani Hale A2

    Waikoloa, HI

    Pool Hot Tub

    $1,137 to $2,743/night

  34. ESTATE
    Ali'i Villa

    Ali'i Villa

    Kailua Kona, HI

    Pool Hot Tub

    $1,137 to $2,029/night

  35. APARTMENT
    Diamond Head Beach Hotel Rooftop 1402

    Diamond Head Beach Hotel Rooftop 1402

    Honolulu, HI

    FREE CANCELLATION

    $1,103/night

  36. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    Pool Hot Tub

    $1,084 to $3,320/night

  37. CONDOMINIUM
    MAKENA SURF RESORT, #G-304

    MAKENA SURF RESORT, #G-304

    Makena, Maui, HI

    Pool Hot Tub

    $1,066 to $1,459/night

  38. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Pool Hot Tub

    $1,065 to $3,608/night

  39. CONDOMINIUM
    Whaler at Kaanapali Beach 852

    Whaler at Kaanapali Beach 852

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  40. CONDOMINIUM
    Whaler at Kaanapali Beach 402

    Whaler at Kaanapali Beach 402

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $1,034 to $1,371/night

  41. VILLA
    Mauna Kea Villas #13

    Mauna Kea Villas #13

    Kamuela, HI

    $1,018 to $1,880/night

  42. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    $996 to $3,151/night

  43. HOUSE
    Punahele Point

    Punahele Point

    Princeville, HI

    $978 to $1,199/night

  44. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Pool Hot Tub

    $977 to $3,083/night

  45. VILLA
    3BD Fairways Villa (116D) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Pool Hot Tub

    $943 to $2,944/night

  46. CONDOMINIUM
    WAILEA ELUA, #1403

    WAILEA ELUA, #1403

    Wailea, Maui, HI

    Pool Hot Tub

    $931 to $1,459/night

  47. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Pool Hot Tub

    $929 to $3,553/night

  48. ESTATE
    Hale Kauka

    Hale Kauka

    Kamuela, HI

    Pool

    $899 to $1,434/night

  49. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    Pool Hot Tub

    $899 to $2,267/night

  50. HOUSE
    Hale Grace Aloha

    Hale Grace Aloha

    Kailua Kona, HI

    Pool

    $887 to $1,138/night

  51. CONDOMINIUM
    Honua Kai-Konea #925

    Honua Kai-Konea #925

    Lahaina, HI

    Pool
    FREE CANCELLATION

    $858 to $2,564/night

  52. CONDOMINIUM
    MAKENA SURF RESORT, #E-205

    MAKENA SURF RESORT, #E-205

    Makena, Maui, HI

    Pool Hot Tub

    $855 to $1,319/night

  53. CONDOMINIUM
    MAKENA SURF RESORT, #B-304^

    MAKENA SURF RESORT, #B-304^

    Makena, Maui, HI

    Pool Hot Tub

    $855 to $1,319/night

  54. CONDOMINIUM
    Whaler at Kaanapali Beach 723

    Whaler at Kaanapali Beach 723

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $849 to $1,169/night

  55. CONDOMINIUM
    Whaler at Kaanapali Beach 1173

    Whaler at Kaanapali Beach 1173

    Lahaina, HI

    Pool Hot Tub
    FREE CANCELLATION

    $849 to $1,169/night

  56. CONDOMINIUM
    MAKENA SURF RESORT, #B-204

    MAKENA SURF RESORT, #B-204

    Makena, Maui, HI

    Pool Hot Tub

    $841 to $1,319/night

  57. CONDOMINIUM
    WAILEA ELUA, #1002

    WAILEA ELUA, #1002

    Wailea, Maui, HI

    Pool Hot Tub

    $841 to $1,515/night

  58. CONDOMINIUM
    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua Bay Villa 22G2 Gold Ocean Front

    Kapalua, HI

    Pool

    $813 to $1,219/night

  59. HOUSE
    Hale Pulelehua TVNC#1238

    Hale Pulelehua TVNC#1238

    Hanalei, HI

    $809 to $1,771/night

  60. CONDOMINIUM
    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    Kailua Kona, HI

    Pool

    $809 to $2,505/night

  61. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    FREE CANCELLATION

    $790 to $1,051/night

  62. CONDOMINIUM
    WAILEA ELUA, #1204^

    WAILEA ELUA, #1204^

    Wailea, Maui, HI

    Pool Hot Tub

    $785 to $1,347/night

  63. CONDOMINIUM
    WAILEA ELUA, #1702

    WAILEA ELUA, #1702

    Wailea, Maui,, HI

    Pool Hot Tub

    $785 to $1,347/night

  64. CONDOMINIUM
    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua Bay Villa 21G2 Gold Beach Front

    Kapalua, HI

    $781 to $1,219/night

  65. CONDOMINIUM
    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua Bay Villa 30B3 Ocean Front

    Kapalua, HI

    $781 to $1,219/night

  66. CONDOMINIUM
    Kapalua Bay Villa 35B3 Gold Ocean Front

    Kapalua Bay Villa 35B3 Gold Ocean Front

    Lahaina, HI

    Pool

    $781 to $1,219/night

  67. CONDOMINIUM
    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua Bay Villa 34B2 Gold Ocean Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  68. CONDOMINIUM
    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua Bay Villa 20G2 Gold Beach Front

    Kapalua, HI

    Pool

    $781 to $1,219/night

  69. HOUSE
    Plantation Cottage at Poipu

    Plantation Cottage at Poipu

    Koloa, HI

    Pool Hot Tub

    $780 to $1,910/night

  70. CONDOMINIUM
    MAKENA SURF RESORT, #G-201*

    MAKENA SURF RESORT, #G-201*

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  71. CONDOMINIUM
    MAKENA SURF RESORT, #F-212

    MAKENA SURF RESORT, #F-212

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  72. CONDOMINIUM
    MAKENA SURF RESORT, #G-101

    MAKENA SURF RESORT, #G-101

    Makena, Maui, HI

    Pool Hot Tub

    $775 to $1,094/night

  73. HOUSE
    Hale Honu-Oceanfront

    Hale Honu-Oceanfront

    Kailua Kona, HI

    Hot Tub
    FREE CANCELLATION

    $766 to $846/night

  74. CONDOMINIUM
    MAKENA SURF RESORT, #G-104

    MAKENA SURF RESORT, #G-104

    Makena, Maui, HI

    Pool Hot Tub

    $762 to $1,094/night

  75. CONDOMINIUM
    Mauna Lani Terrace D201

    Mauna Lani Terrace D201

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,395/night

  76. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $934/night

  77. HOUSE
    Hokulani Villa

    Hokulani Villa

    Princeville, HI

    Pool

    $750 to $2,113/night

  78. HOUSE
    Malapua

    Malapua

    Hanalei, HI

    FREE CANCELLATION

    $748 to $1,060/night

  79. HOUSE
    Blue Hawaii

    Blue Hawaii

    Kailua Kona, HI

    Pool

    $744 to $2,568/night

  80. CONDOMINIUM
    Hale Lalea Ko Olina Beach Villa (B310)

    Hale Lalea Ko Olina Beach Villa (B310)

    Kapolei, HI

    Pool Hot Tub

    $740 to $2,021/night

  81. VILLA
    3BD Wai'ula'ula Villa (345) at Mauna Kea Resort

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    Kamuela, HI

    Pool Hot Tub

    $738 to $2,169/night

  82. CONDOMINIUM
    WAILEA ELUA, #0908

    WAILEA ELUA, #0908

    Wailea, Maui, HI

    Pool Hot Tub

    $724 to $1,065/night

  83. CONDOMINIUM
    WAILEA ELUA, #2304

    WAILEA ELUA, #2304

    Wailea, Maui, HI

    Pool Hot Tub

    $724 to $1,065/night

  84. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $720 to $1,717/night

  85. HOUSE
    Nai'a Hale

    Nai'a Hale

    Kailua Kona, HI

    FREE CANCELLATION

    $719 to $1,411/night

  86. HOUSE
    Hale Koaniani

    Hale Koaniani

    Wainiha, HI

    FREE CANCELLATION

    $717 to $904/night

  87. HOUSE
    Mauna Lani KaMilo Home (349)

    Mauna Lani KaMilo Home (349)

    Kamuela, HI

    Pool Hot Tub

    $706 to $2,142/night

  88. CONDOMINIUM
    Hale Ili Ili #A

    Hale Ili Ili #A

    Kihei, HI

    Pool Hot Tub
    FREE CANCELLATION

    $695 to $1,043/night

  89. HOUSE
    Ohana Kamalani

    Ohana Kamalani

    Princeville, HI

    Pool

    $690 to $1,702/night

  90. HOUSE
    Lokelani Hale

    Lokelani Hale

    Hanalei, HI

    FREE CANCELLATION

    $686 to $873/night

  91. HOUSE
    Hale A Kai

    Hale A Kai

    Princeville, HI

    FREE CANCELLATION

    $686 to $936/night

  92. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Pool Hot Tub
    FREE CANCELLATION

    $680 to $1,236/night

  93. HOUSE
    Ali'i Point #5 Oceanfront

    Ali'i Point #5 Oceanfront

    Kailua-Kona, HI

    Pool
    FREE CANCELLATION

    $668 to $846/night

  94. CONDOMINIUM
    Hale Akala Falls Ko Olina Beach Villa (O121)

    Hale Akala Falls Ko Olina Beach Villa (O121)

    Kapolei, HI

    Pool Hot Tub

    $664 to $1,673/night

  95. CONDOMINIUM
    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua Bay Villa 21G4 Gold Beach Front

    Kapalua, HI

    Pool

    $656 to $875/night

  96. CONDOMINIUM
    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua Bay Villa 21G5 Gold Beach Front

    Kapalua, HI

    Pool

    $656 to $906/night

  97. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club 5-304

    Keauhou Kona Surf and Racquet Club 5-304

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $651 to $717/night

  98. HOUSE
    Turtle Rock

    Turtle Rock

    Kailua Kona, HI

    Pool
    FREE CANCELLATION

    $641 to $934/night

  99. HOUSE
    WAILEA ELUA, #1309

    WAILEA ELUA, #1309

    Wailea, Maui, HI

    Pool Hot Tub

    $634 to $896/night

  100. HOUSE
    Hale Anu Keanu

    Hale Anu Keanu

    Princeville, HI

    Hot Tub

    $631 to $1,868/night